6108-63-0Relevant academic research and scientific papers
Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides
Johnson, Keywan A.,Biswas, Soumik,Weix, Daniel J.
supporting information, p. 7399 - 7402 (2016/05/24)
An improved method for the reductive coupling of aryl and vinyl bromides with alkyl halides that gave high yields for a variety of substrates at room temperature with a low (2.5 to 0.5 mol %) catalyst loading is presented. Under the optimized conditions, difficult substrates, such as unhindered alkenyl bromides, can be coupled to give the desired olefins with minimal diene formation and good stereoretention. These improved conditions also worked well for aryl bromides. For example, a gram-scale reaction was demonstrated with 0.5 mol % catalyst loading, whereas reactions at 10 mol % catalyst loading completed in as little as 20 minutes. Finally, a low-cost single-component pre-catalyst, (bpy)NiI2 (bpy=2,2′-bipyridine) that is both air- and moisture-stable over a period of months was introduced.
Stereoretentive Pd-catalyzed kumada-corriu couplings of alkenyl halides at room temperature
Krasovskiy, Arkady L.,Haley, Stephen,Voigtritter, Karl,Lipshutz, Bruce H.
, p. 4066 - 4069 (2014/10/15)
Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing β-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.
Ligand effects on the stereochemical outcome of suzuki-miyaura couplings
Lu, Guo-Ping,Voigtritter, Karl R.,Cai, Chun,Lipshutz, Bruce H.
experimental part, p. 3700 - 3703 (2012/06/15)
The ligands associated with various Pd catalysts play a crucial role in determining the stereochemistry of cross-couplings between boronic acids and Z-alkenyl halides. A ligand on palladium has been found that leads to the desired products under mild conditions and in high yields that, in most cases, retain their Z-olefin geometry.
Ligand effects on Negishi couplings of alkenyl halides
Krasovskiy, Arkady,Lipshutz, Bruce H.
supporting information; experimental part, p. 3818 - 3821 (2011/10/01)
Negishi couplings at olefinic centers do not always occur with the anticipated maintenance of stereochemistry. The source of erosion has been traced to the ligand, and a modified method has been developed that solves the stereochemical issue and significantly improves yields of Negishi couplings in general.
